My Cross-Dressing Secretary

A request from the author: English is not my first language, and although I have written many articles in English, I still have a vocabulary failures especially in the sexual field. I would be happy if any of my readers, for whom English is a first language, would volunteer to read my stories before publication, and suggest language corrections. Provided he has free time and can respond quickly.

*****

I hate jogging.

For years, the only sport I did was lifting weights twice a week at the gym. About a year ago, my home weight warned I gained 3 kilos. When I was younger, I was an outstanding swimmer and even won several medals in local competitions, and because I hate jogging, I went back to swimming. I purchased a subscription to the public swimming pool and every morning, as soon as the pool opens at 5:30 am, I arrive and swim 5 miles.

The advantage of swimming in the early morning is that the pool is empty. In fact, I'm the only man in the pool. Apart from me, only 6 other aunties come regularly at this early hour. I call them aunties, but they are older women between the ages of 50 and 65. For comparison, I am 45 years old.

I have to say to the credit of the aunties that they really do swim. Not as far as I, but they swim, not only talk. Oh yes, they also talk, of course. Mostly about me. I see them gossip, looking at me with sparkling eyes and examining my body.

After my pool quota, I lie down a bit in the small jacuzzi pool to let my muscles relax. As soon as I go out to the hot tub, two or three more aunties join in, and within five minutes all the aunties are with me. The hot tub is not for seven people, so once all of them join me, the "seemingly random" touches begin. You know, the currents shift the body a little bit one way or the other, and some leg suddenly rubs against my leg, or some auntie actually sticks to me.

Totally transparent these aunties.

After a year, we formed a sense of brotherhood and mutual agreement -- they know they don't have a chance with me, but they know I'll let them fantasize freely. A week ago, on my birthday, one of my aunties even brought a cake.

This morning, an anomaly occurred in this regular ritual -- as I exited the pool, I met a young blond guy who had just arrived. I didn't know him, but he probably knew me. He smiled greetingly at me and said, "Good morning, Mr. Ryan."

He seemed like a nice guy, so I stopped and asked, "Did we meet?"

"You may not remember me," he replied. "I'm friends with Billy, your son, from college. How's the pool here?"

"Nice," I replied. "And what's your name?"

"I'm Alan."

"Okay, Alan. Have a good morning and enjoy the pool." I said and continued my way to the adjacent parking lot.

Like every morning, I got home, had my second coffee, woke up my wife, and then went to wake Billy. We also have an older daughter, Kelly, but she's in college and lives in a dorm. I walked into Billy's room and the first thing that came to my mind was, "What is Kelly doing in Billy's bed?"

This, of course, was not Kelly but Billy. He lay on his stomach, completely naked, his smooth white butt on display. I slapped him on his butt and said, "Good morning, sleepy. Since when are you going to bed naked?"

"Morning, Dad. I was totally drained last night."

"Well, breakfast in fifteen minutes on the clock."

Of course, he didn't arrive on time, so I had to leave for the office before I could tell him I had met his friend.

*****

The next morning, Alan arrived just after me. When I left the cloakroom, he came in and greeted me cordially, as if we were old friends: "Good morning, Mr. Ryan. Going to rip off the pool?"

I smiled politely and didn't reply.

I did my pools and went out to the hot tub. One after the other, all the aunties arrived. Alan came last. He was squeezed in front of me between two aunties who were happy to make room for him. The crowding was already very high, which was a convenient excuse for Inez, on my right, to cling to me. To my left was Susan, the youngest and probably the shyest of them all. She was still trying to maintain a semblance of false modesty.

The warm currents form a foam on the surface of the water, so you can't clearly see what's going on underwater, but I was willing to swear that the two aunties opposite, the ones sitting on either side of Alan, were less modest. Alan himself seemed indifferent to their touch. He lay with his eyes closed, completely ignoring the aunties beside him.

I got up from the hot tub and went to take a shower. In a public pool, as in a public pool, the showers are not closed. The men's shower room is a rectangular room, five open showers on each side. I shower efficiently, and don't waste time showering. So as soon as I went underwater, I started washing my head. A few minutes later, Alan arrived. He grabbed the shower in front of me and enjoyed the hot water.

I didn't pay much attention to him until I noticed that he was surveying my body, the same way the aunties were surveying it. I looked back at him, and he didn't look down. Just smiled. within myself, I had to admit that he had a beautiful body. Not a beautiful male body, but a beautiful female body. His golden skin was completely smooth, and I wondered if he was shaving, or if he hadn't matured yet.

In the coming days, Alan became an integral part of the pool fraternity. I watched him swim. He swam well, in long, strong movements, with his smooth female body moving through the water like an eel. He also swam fast and I had no doubt that under the soft female body there were strong muscles.

In the hot tub he always sat more or less in front of me, but in the shower, he always took a shower right in front of me. The little cheeky one stared at my body with his blue, dreamy, shameless eyes. Always when I looked back at him, he just smiled. He made caressing movements as if he were masturbating, and I found myself contemplating what it would be like to caress this beautiful body.

This morning he also had the onset of an erection. His penis was medium minus, and pretty thin either, but beautiful, straight, circumcised and smooth. And... suddenly I noticed that he had no hairs above it. Well, of course he shaves. I wondered if his erection is because of me, and an unpleasant shiver ran through my body.

A week later, he introduced me to his butt. Until that morning, he had always showered facing me, but this time he turned around and showed off his round, erect butt. From the back he completely looks like a woman. Actually, sexy young girl. After showing me his butt, he bent down, as if to soap his legs' calves, letting his butt open and show his anus.

Until I saw the little bastard's anus, I didn't understand what all the sex stories mean when they describe the asshole with the word "rose." But his anus certainly looked pinkish, cramped and beautiful. He turned to me, smiled and said, "Mr. Ryan, you have a nice cock."

The little cheeky.

I didn't even notice that his beautiful butt's sight, with a rose in the center, made me a boner. He surely didn't miss it. I was surprised and didn't know how to react. In retrospect, I know I should have responded harshly, or at least with witty cynicism, something like, "Yes, all women tell me that." But I just fell silent. Believe me, it doesn't happen to me much that suddenly I can't find words to respond.

Fortunately, at the exit from the pool, I met Inez, the cheekiest of all the aunties.

"Inez, I need something from you. Want a ride?"

She was sure I wanted to court her and replied with obvious joy. We got into my car, and I asked, "What do you think of Alan?"

She was surprised. That's not how she thought the conversation would go.

"Nice guy," she replied noncommittally.

"I want to ask you for something. Can you court him? Or make sure one of the girls lay him down?"

"Timothy Ryan," she replied reproachfully, "we're not girls for hire."

"Inez, enough with the craps," I said. "I'm sure more than one of the girls would love to make love with him and I'm willing to make a deal with you -- if you give him a fuck, you get a fuck from me. How's that?"

Her false modesty was completely gone, and she asked suspiciously, "Where's the catch?"

"There's no catch," I said. "I promise you a heavenly orgasm. I'll invest effort in you, Inez."

*****

Two more weeks passed, and nothing have changed, except Alan was getting more bolder. In the hot tub, he occasionally sat down next to me, letting me feel his silky skin; and he no longer satisfied with demonstrating his butt or anus, but also caressed his butt while soaping it, as working extra hard to clean its hole, stroking it in circular motions with a soapy finger.

I no longer had any doubt that the little bastard was trying to seduce me.

I hate to say, but it kind of worked for him, because every time he had his back to me, I fantasized about a young girl. In fact, if we ignore his dick, every girl would love a body as soft, shapely and pleasant as his. His smooth body made me harden more than once and every time he caught me with an erection, he complimented me. To hide my erection, I turned with my back to him, and deep down I decided that if the little cheeky complimented my butt, I would slap him, even if he would sue me for assault.

And there were also days when during the day I couldn't get his beautiful body out of my mind.

During these two weeks, I also caught Billy sleeping completely naked, with his butt showcased, more than once. For a moment I wondered if there was a connection between the two, but it was hard to me to believe. Billy was also pretty and smooth, but as far as I know, he has a girlfriend and he's totally straight. But the combination of Billy's white butt and Alan's beautiful rose, pierced my mind and infused it with thoughts I hadn't thought of before.

After two weeks, Inez gave up. She sat next to me in the hot tub and whispered to me: "Sweetie, the boy is a gay. Anything for me for the effort?"

I wasn't sure that the fact that the aunties couldn't seduce him was evidence that he was gay, they couldn't seduce me either. I promised her to think about it, but she didn't give up.

"At least let me suck you," she said.

"And what will it give you?" I asked.

"Sweetheart, at my age even feeling your dick swelling in my mouth can make me orgasm."

So, we decided that today I would give her a ride to her home...

*****

The next day, Alan sat down in the hot tub right next to me and rubbed against me shamelessly. His hand fell on my thigh more than once, and on one occasion he seemed to fall to the side while turning his butt toward me. I decided it was time to teach the cheeky a lesson.

*****

I waited for the right opportunity, and it came a few days later. Alan turned his butt to me and soaped his anus. My erection was almost full. I soaped my dick and as soon as he bent down to his calves, I stood behind him pressing it into his asshole.

He was slammed against the shower wall, braking himself with both hands. I pressed my cock against his ass and muttered, "You said you liked my cock, didn't you?"

"Yes, Mr. Ryan. I love it. But I've never done that before, so please be gentle."

Don't get me wrong. Anal sex was nothing new to me. I've done this dozens of times, with my wife and other women before her. But the thought that it was a guy and not a girl, added a stimulating psychological dimension to the act; The fact that I surprised him, maybe even raped him, added another psychological dimension; And his young, pleasant, and strong, body was another unique addition to the fuck.

I cupped both of his cheeks and spread them, pushing my hard rod against the contracted muscle of his asshole and I barely inserted the head of my prick. The feeling of his butt inside my hands was pleasant. He pressed his butts together, trapping my cock between them. The cramped butt was hard as stone, which didn't surprise me. I knew he was strong.

I slapped his butt and whispered in his ear, "Release."

He tried to release both his butt and anus and I was able to insert my dick a bit more into him. I shook his cheeks, massaging with it my rod that still out and it felt wonderful. Like breasts fucking.

He leaned against the wall and pushed himself back, determined to fully accept my cock. On this issue, we fully agreed, and I pushed myself into him, too. I hugged his waist and pressed his body against mine. It was like hugging a woman, as if I let my hand go down a little bit, I'd meet a pussy. But when I lowered my hand down, I met, as expected, a cock. It was erect and barely the size of my fist. My touch on his prick made him gasp in surprise and he pushed himself back forcefully, causing my boner to fully penetrate his tight hole. He let out a restrained scream.

"God, that's really good. Mr. Ryan, fuck me, please."

He leaned his body against the wall and rested, I also leaned against his body and rested. I closed the water tap and started fucking. In and out. It wasn't easy and smooth; his hole wasn't lubricated like a woman's pussy. He lifted his head back and whispered to me, "Maybe it would help if you dripped some shampoo on your dick."

"Good idea," I said.

Now we managed to really be fucking. With each penetration, his body shivered as if I had touched some inner clit. His legs stretched and pressed against mine, and his butt shook with some internal trembling. He straightened his back and hugged my head. His ass was narrow and pristine, and the movements of his soft butt drove me completely insane. Again, he tightened his butt on my cock, screwing his tight butt, and the friction was unbearable.

I hugged his body, enjoying the mixture of a strong, hard body wrapped in soft, pleasant skin. It was a strange feeling that I had not yet experienced. I buried my head in his shoulder and licked his neck. He tightened his grip on the back of my neck and whimpered quietly.

"Mr. Ryan," he whispered, "I think I'm going to cum."

"Cum up, whore, but I keep fucking you until I cum too." I replied.

He pushed himself back, pressing his body hard against mine. I felt the contraction of his dick in my hand. I tightened my grip on his small cock, causing his whole body to harden and then to cum in a series of spasms that caused his butt to harden and his asshole to contract on my cock.

He shot several jets of sperm against the shower wall and then let go of my head, collapsing with both hands on the wall.

"Holy shit," he blurted out, "I've never cummed like this."

I grabbed his soft waist and fucked him vigorously. He seemed to recover a bit, as he reached between his legs and grabbed my balls.

"Mr. Ryan, please, cum in my ass," he said.

I think it was this rude statement that closed the deal, because at that moment I felt the orgasm building forcefully in my testicles, climbing to the root of my cock and then causing it a pleasant contraction, followed by strong pulses that filled his intestines with my juice.

I gave myself another moment to relax and then pulled myself out of him. He didn't hesitate for a second, and immediately turned around, pressed his body against mine, grabbed my head and kissed me on the lips.

"Mr. Ryan, do you feel satisfied, or would you like me to suck you?" he asked.

What is there to say, five-star service...

*****

Over the next few days, it became part of my daily ritual--pool, hot tub, fucking Alan's magnificent ass, and then a quick shower and home. If my wife noticed that my sexual demands on her dropped, she didn't say so.

Then Alan came up with a new pose that he learned from watching porn. At the end of the shower room there are always some plastic chairs. He carried a chair and placed it in the last shower, sat me down on the chair and climbed on it, trying to sit on my cock with his back to me. In honor of the new position, Alan made sure to lubricate his asshole well.

He settled on my cock carefully, as I hold it upright for him, and impaled himself on it. I hugged his body, enjoying the touch of his smooth body and soft, pleasant skin. He fully inserted my shaft into him, leaning back on me and pulling my face into a kiss. I still had mixed feelings about kissing a man, but as soon as he massaged my balls, I grabbed his head and kissed him until he was breathless.

"Oh, Mr. Ryan," the little horny gurgled with pleasure, "you're a great fuck."

I grabbed his small dick and massaged it gently. He moaned deeply and went up and down on my cock. Then he did something that drove me crazy. He lifted up so that only the tip of my cock remained inside him, contracting his butt forcefully and moving it in circular motions, giving my prick a full massage from all directions. I felt like I was going to cum.

He went up and down on me a few times, then stopped again and twisted his butt with only my cock's head inside him. His breathing became strong and whole his body shook with unconcealed pleasure. This time right after he stop "spinning", he sat up abruptly, forcefully inserting my hard rod into him. I, unprepared for the rapid movement, was still stretching his member, which was suddenly stretched to double length. He cried out in pain, and immediately gurgled in pleasure.

"God, that must be what they do in heaven all day," he said.

The third time he did his little exercise, I couldn't help myself anymore. All the sperm that had accumulated in my testicles was emitted into his intestines in long jets accompanied by long, strong contractions.

It was a great orgasm.

His already hard little dick was still in my hand. I rubbed it with my hand as he wiggled his beautiful ass on my cock which kept dripping into his ass. Moments later, he cummed and his whole body shook from the intensity of the orgasm. The only downside was that all his sperm spilled on my hand. I opened the shower and washed my hand with the running water.

He leaned his body against me and tilted his head against mine. I took his face and kissed him, sticking my tongue deep into his mouth. I caressed his smooth stomach and moved up to his soft chest, pinching his nipples.

"Mr. Ryan," he whispered in my ear. "I want to be your girlfriend."

I froze. My girlfriend?

"And that means... What exactly?" I asked.

"That once in a while we'll fucking on a bed. We'll make love, play foreplay and cum a few times. Every time you cum, I'll suck you, so you'll be able to fuck me again."

"You know I can't bring you home," I said.

"I know. But maybe..."

I stopped him. It was getting late, and I was afraid someone would surprise us.

"Hold that thought. Someone might come in. Let's get out and I'll buy you a cup of coffee, and we'll try to figure out how you can be my girlfriend," I said.

As we exited the building, we met Inez, and she seemed to be waiting for me.

"Mr. Ryan," she began, "can you give me a ride home?" Her sparkling eyes made it clear exactly what the purpose of the ride will be.

"Not today, sweetheart," I replied. "I'm in a bit of a hurry home."

Alan, who was walking a few steps behind me, rushed over to me and said, "Mr. Ryan, maybe I can join you? I arranged with Billy that we would work together in the library today."

"No problem," I replied, complimenting his resourcefulness and quick response.

We went out, and on the way he asked, "How old do you think Inez is?"

"I guess something around 60. Why?"

"She's pretty reserved," he said.

"Everyone there is reserved. Swimming keeps them in shape."

"Who's the oldest one?"

"In my opinion, it's Clara. She's just retired, so she's probably between 62 and 66."

Alan chuckled loudly and I asked, "What's funny?"

"Just. She looks better than Inez."

On the way we stopped in a small café that served breakfasts. We were seated and I suggested him to order. I settled for coffee.